Acid salts of p-aminobenzene sulphonyl guandine



Patented Feb. "4, 1941 UNITED STATES PATENT OFFICE 9mm 5 Y SULPHONYL GUANIDINE Philip Stanley Winnek, Riverside, Com, asslznor to'Amei-ican .Oyanamld Company, New York, N. Y., a corporation of Maine No Drawing.

6 Claims.

The present invention relates to the salts of p-aminobenzene sulphonyl guanidine.

5 since that compound is claimed in my copending application Serial No. 320,430 filed February 23, 1940, which matured into U,= S. Patent 2,218,490 on October 15, 1940, of which the present application is a continuation in part.

1 The compounds of this invention are useful as chemotherapeutic agents and also asintermediates in the preparation of other compounds.

The p-aminobenzene sulphonyl guanidine base 25 zone sulphonyl guanidine is sumciently basic in reaction to combine with any inorganic or organic acid and form salts therewith. The ordinary inorganic salts, such as the hydrochlorides, sulphates, phosphates, chlorates and the like may be prepared by adding p-aminobenzene sulphonyl guanidine to a relatively strong aqueous solution of the acid. A salt produced by the reaction may be very conveniently recovered by diluting the aqueous solution with an organic solvent such as acetone and recovering the resulting precipitate by filtration. The salts of the water soluhie organic acids, such as for example acetic, lactic, citric, and the like, may be prepared as described in the process above. Another suitable method for preparing the salts comprises a, methed in which a relatively water insoluble organic acid, such as benzoic, is dissolved in an organic solvent, for example ethyl alcohol, and the paminobenzene sulphonyi guanidine added to this solution, in which case the salt may be recovered by any convenient means as for example by evapcrating the solution to dryness. Still another method for preparing salts in accordance with The 'p-- aminobenzene sulionyl guanldine compound as the free base is not claimed in this application used in making the salts of this invention' may organic acid, for example, sodium phthalate, also Application September 19, 1940, Serial No. 357.501

preferably in aqueous solution and the acid salt separated from the sodium chloride.

It is readily seen, therefore, that the present invention relates to and includes any inorganic acid salt. similarly this invention includes any organic acid salt of p-aminobenzene sulphonyl guanidine including the saturated andunsaturated hydroxy, halogenated or other substituted acids of the aliphatic, alicyclic, aromatic, and heterocyclic series. Preferably the salts are those m produced from relatively non-toxic organic acids or those having some bactericidal or other therapeutic property, including acids such as acetic, salicylic, mandelic, lactic, and the like.

The invention will be described in greater detail in conjunction with the following specific examples which are merely illustrative of suitable methods ior preparing representative compounds of the class and are not intended to limit the scope of the invention. Parts are by weight except in the case-.01 liquids which are expressed in corresponding gfiarts by volume.

Example 1 Example 2 One part of p-aminobenzene sulphonyl guanidine was added to 2 parts of 95% phosphoric acid and heated just to boiling, cooled and filtered. The salt obtained was a white crystalline product soluble in water.

Example 3 6 parts of p-aminobenzene sulphonyl guanidine dissolved in 60 parts of hot water were added to 3 parts of salicylic acid dissolved in 100 parts of hot water, cooled and filtered, The salt obtained was a white crystalline product soluble in boiling water.

Ewample 4 One part of p-aminobenzene sulphonyl guanidine was dissolved in 2 parts of hot concentrated sulphuric acid, cooled, and acetone added to precipitate. The suspension was filtered. The sulphate obtained was a white crystalline solid, in-

soluble in acetone but soluble in cold water.

Example 5 5 parts of mandelic acid was added to 48 parts or 10% sodium hydroxide and sumcient water was added to make a hot solution. The two solutions were mixed and a white crystalline product soluble in hot water was obtained. After 0001- 0 ing the salt was recovered by filtration.

What Iciaimis:

1. Acid salts of p-aminobenzene sulphonyi guanidine.

-phonyl Buanidine.

2. Inorganic acid salts of-p-aminobenzene sulphonyl :uanidine.

3. Organic acid salts oi p-aminobenzene sulh4.tep-.iminobenzene suiphonyi guanidine phosp a e 5. p-Aminobenzene aulphonyl guanidine lactate.

8. p-Aminobenzene 'sulpiionyl guanidine salicylat'e.

PHILIP STANLEY WINNEK. 

